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Chester VT Real Estate

Located in Windsor County, Chester is a wonderful New England town reminiscent of a bygone era. With architecture pre-dating the civil war, Chester is rich in history and beauty. Although historic, the quaint town is thriving with its unique markets, galleries, and restaurants that offer much to do. The town is also conveniently located close to Okemo Mountain and Mount Snow for those who enjoy outdoor recreation as well as within driving distance to Manchester, VT

Search the latest real estate in Chester, VT with Maple Sweet Real Estate. Find the right property for you from a variety of listings. To save your favorites, register with us and you can get email notifications when similar properties are posted. Already have an account with us? Log in here.

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683 Church Street Chester VT 05143

Chester, VT683 Church Street

Price$1,750,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4932616

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 6
  • Square Feet 5,566

Spectacular 7-bedroom country home on 45+/- acres located in Chester, Vermont. This luxurious home combines the beauty of its architectural features with its magnificent country setting. Starting in the kitchen, there is an open kitchen design, large center island, a breakfast bar, a pantry with an additional oven and wine cooler, an oversized kitchen sink, and a commercial grade oven fit for a chef. In the living room there is an amazing stone fireplace with vaulted ceilings, an open post and beam design, and floor to ceiling windows. The dining room is sizeable and could be a perfect place for friends and family to gather for a meal. The main level has two bedrooms located near the back of the home. Both include their own private bathrooms. There is another half bathroom near the mudroom. Upstairs, above the three-car garage, there is a spacious primary suite with a full bath and walk-in closet. On the second floor there are three bedrooms, two of those bedrooms share a beautiful bathroom and the other bedroom has its own private bath. There are two lofted areas on the second floor. One of the lofts is spacious enough for a pool table and an extra living room space. This home includes 4 wood burning fireplaces, 1 outside fireplace and, 2 wood burning stoves. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Listed by Katherine Burns of William Raveis Vermont Properties

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

465 Pennell Road Chester VT 05143

Chester, VT465 Pennell Road

Price$1,685,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4918189

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4,444

This extraordinary residence and property is located in the vibrant community of Chester. Chester is easily accessed from Interstate 91 and is the gateway to Vermonts best ski areas which create an abundance of exceptional restaurants, cultural events and recreational options. The property is a south facing, very private 79 acres which consists of well maintained woodlands including a sugarbush with a state of the art sugarhouse and open meadows in the forefront of long range views. Located just below the residence is a large swimming, fishing pond with an adjacent lighted tennis court. Trails for hiking, cross country skiing and mountain biking are throughout the property. Truly an exceptional private setting that has been enhanced by the residence which is expertly sited to take in all that the property offers. The residence was designed and built by the owner who is a renowned wood craftsman. The level of craftsmanship displayed throughout the house is without equal. The choicest woods combined with incredible execution make for a truly unique environment. Every room and space in the house is warm and inviting while offering efficiency and sustainability. Combine this with state of the art systems and unexpected amenities including an adult sized and scaled treehouse make this property a must see for the discerning buyer. You won't be disappointed.

Listed by Wade Treadway of Wade I Treadway Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

141 Stage Road Chester VT 05143

Chester, VT141 Stage Road

Price$924,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4822981

  • Land
  • Acreage 509.73
  • Area Near Skiing, Rural
  • Utilities None
  • Zoning Residential

Don't miss the rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning 509+/- acres has it all. Made up of 4 contiguous preexisting lots the parcel has road frontage on Stage Road in Chester giving multiple opportunities for a number of small subdivisions. Three lots also front onto route 35 between Chester and Grafton which includes two 70 +/- acres lots. There are also gravel deposits on the site which could be used to develop the logging trails further. If you have conservation on your mind the entire lot is enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded and hosts a large open area for staging a logging operation. There are also a network of marked logging trails throughout the property making it easily accessible. The beautifully crafted ponds offer a welcome spot to take in the beauty of the landscape as well attracting all manner of wildlife. The seller will entertain selling individual lots separately. Whether you wish to develop or keep this pristine site as is you will find endless choices and opportunity for this very special place. Come see today!!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Stage Road Chester VT 05143

Chester, VTStage Road

Price$622,650The price has recently decreased

Est. Mortgage: $/month

MLS Number 4931759

  • Land
  • Acreage 296.5
  • Area Near Skiing, Rural
  • Utilities None
  • Zoning Residential

Rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning property has it all. Made up of 3 contiguous preexisting lots with a right of way via Stage Road in Chester giving multiple opportunities for a number of small subdivisions. Three lots also front onto route 35 between Chester and Grafton which includes two 70 +/- acres lots. There are also gravel deposits on the site which could be used to develop the logging trails further. If you have conservation on your mind the entire lot is enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded and hosts a large open area for staging a logging operation. There are also a network of marked logging trails throughout the property making it easily accessible. The beautifully crafted ponds offer a welcome spot to take in the beauty of the landscape as well attracting all manner of wildlife. The seller will entertain selling individual lots separately. Whether you wish to develop or keep this pristine site as is you will find endless choices and opportunity for this very special place. Come see today!!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

12 Common Street Chester VT 05143

Chester, VT12 Common Street

Price$495,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4929151

  • Multifamily
  • Units 3
  • Bathroom 2
  • Acreage 0.25
  • Square Feet 4,060

Located at the head of the Village Green, it has been home to many successful businesses! The beautiful post and beam interior is warm and inviting. Enjoy the high foot and vehicle traffic in a very desirable area which has long benefitted owners and their businesses. There are 3 units with much potential! The first being the business store front, second is a space in the back which could easily be turned into a rental with a kitchen and separate bathroom, the third is a second floor 2 bedroom 1 bathroom with much potential! Along with the many benefits of this properties location comes parking right on the Green. Some recent updates are the back portion on the building has a new roof and solar was added to the whole building recently as well. Owner may consider owner financing.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

12 Common Street Chester VT 05143

Chester, VT12 Common Street

Price$495,000The price has recently decreased

MLS Number 4928621

  • Commercial
  • Year Built 1820
  • Square Feet 4,060
  • Acreage 0.25

Located at the head of the Village Green, it has been home to many successful businesses! The beautiful post and beam interior is warm and inviting. Enjoy the high foot and vehicle traffic in a very desirable area which has long benefitted owners and their businesses. There are 3 units with much potential! The first being the business store front, second is a space in the back which could easily be turned into a rental with a kitchen and separate bathroom, the third is a second floor 2 bedroom 1 bathroom with much potential! Along with the many benefits of this properties location comes parking right on the Green. Some recent updates are the back portion on the building has a new roof and solar was added recently as well. Owner may consider owner financing.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

81 Main Street Chester VT 05143

Chester, VT81 Main Street

Price$479,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4929143

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,864

Welcome to 81 Main Street! Built in 1820 and located in the heart of the Chester village, this property is historically known as the Guy Earle House and has been a year round vacation home and short term rental property. This quintessential VT gem on .44 acres+/- features 5 bedrooms and 4 baths. Among it's many attractive features are a large living room with wood burning fireplace, formal dining room, two first floor bedrooms, one en suite and an additional bathroom. The 2nd floor includes a large living area, en suite bedrooms, a bonus game room with a handsome wet bar, hand-crafted from school benches. and a pellet stove. Additional Features include: first floor laundry, mudroom/workshop and unfinished attic space. The double lot has generous parking, an oversized 1 car detached garage with potential space to be finished and a separate shed for gardening in the large level yard. The 4 porches adorning the house offer outdoor covered gathering spaces. Stroll to the green for coffee and browse the shops. Close to 5 ski areas, recreational activities and year round fun! Also listed as Commercial see mls# 4937012

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

81 Main Street Chester VT 05149

Chester, VT81 Main Street

Price$479,000The price has recently decreased

Active With Contract

MLS Number 4937012

  • Commercial
  • Year Built 1880
  • Square Feet 4,264
  • Acreage 0.44

Welcome to 81 Main Street! Built in 1820 and located in the heart of the Chester village, this property is historically known as the Guy Earle House and has been a year round vacation home, short term rental property, dance studio and psychologist's office. This quintessential VT gem on .44 acres+/- features 5 bedrooms and 4 baths. Among its many attractive features are a large living room with wood burning fireplace, formal dining room, two first floor bedrooms, one en suite and an additional bathroom. The 2nd floor includes a large living area, en suite bedrooms, a bonus game room with a handsome wet bar, hand-crafted from school benches and a pellet stove. Additional Features include: first floor laundry, mudroom/workshop and unfinished attic space. The double lot has generous parking, an oversized 1 car detached garage with potential space to be finished and a separate shed for gardening in the large level yard. Has been used as owner occupied with 2 commercial units. Close to 5 ski areas, recreational activities and year round fun! Also listed as mls#4129143.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

723 Chandler Road Chester VT 05143

Chester, VT723 Chandler Road

Price$469,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4941297

  • Residential Single Family
  • Bathroom 2
  • Construction Existing
  • Bedrooms 3
  • Square Feet 3,313

A "must see" family home situated on 4.8 private acres on a quiet road, convenient to Chester, Springfield and fifteen minutes to Ludlow and Okemo Ski Resort! Beautifully landscaped with the addition of varietal apple trees in 2022, plenty of open, yard space for vegetable gardens, beautiful stone walls and ample woods surround this ranch-style home in a park-like setting. Quality construction, built with efficiency and low maintenance in mind, offering an open floor design and cathedral ceilings. The main floor features two bedrooms with over-sized closets and two baths, a large, comfortable living room with a new pellet stove opens to the dining area, a nicely appointed kitchen with custom cabinets, double wall oven, ample work space and an island. The second level features an oversized bedroom or bonus room/office. Three mini-split systems were recently added, two on the main floor and one on the second level, providing additional heating options and the comfort of air conditioning. There is a full basement, partially finished, featuring a family/entertaining room with a bar area, as well as a workout space...some gym equipment will be included. There is plenty of additional storage and workshop space, as well. Attached is the heated, two car finished garage with insulated walls, epoxy flooring, and work tub with water; overhead storage available. Shed on concrete foundation in the backyard. This beautiful home is move-in ready...a must see! Showings begin 1/22 at 12noon.

Listed by Suzanne Garvey and McLaughlin Team of Mary W. Davis Realtor & Assoc.,Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1377 Vtrt 103 Chester VT 05143

Chester, VT1377 Vtrt 103

Price$400,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4871606

  • Multifamily
  • Units 2
  • Bathroom 2
  • Acreage 3
  • Square Feet 2,280

Chester Vt 1377 VTRT 103. , Multi Family , Many good uses for property. One and two-family residential and professional office, retail store if it were a home occupation or home business.

Listed by Michael England of Michael England Real Estate

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

32 VT Route 10 Chester VT 05143

Chester, VT32 VT Route 10

Price$379,000The price has recently decreased

MLS Number 4905205

  • Commercial
  • Year Built 1980
  • Square Feet 3,306
  • Acreage 9.4

Outstanding business location! This great 9.4 acre parcel has retail space, walk-in refrigerator and freezer, and a commercial kitchen at ground level, with residential space above for owner/operator or staff! The property is located at the intersection of two state highways - Route 10 and Route 103 which provides excellent access for motorists and tourists. Permitting allows seating for 22. Imagine your local farm to table eatery, a great burger place or maple creamery with activities in the field - perhaps even a 4-wheeler and snowmobile track. This property has amazing possibilities! Bring your passion and imagination when you come see this prime location. Schedule a showing today!

Listed by Suzanne Garvey and Matthew Bellantoni of Mary W. Davis Realtor & Assoc.,Inc.

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Grafton Road Chester VT 05143

Chester, VTGrafton Road

Price$360,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4903171

  • Land
  • Acreage 142.1
  • Area Near Skiing, Rural
  • Utilities None
  • Zoning Residential

Don't miss the rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning 142.1 +/- lot is made up of two separate but adjoining parcels, one in Chester comprising of 70.1 acres and 72 acres in Grafton. Each has road frontage on onto route 35 between Chester and Grafton. If you have conservation on your mind both parcels are enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded with small ponds on the Chester lot. There are also a network of logging trails throughout the property. Come see today!!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.13% last updated on 2023-01-26

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity

Copyright 2023 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated January 31, 2023 3:54 AM EST.

 

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